Four Last Minute Labor Day Trips from Chicago

Summer’s nearly over and you don’t have any Labor Day weekend plans yet? Not to worry. We’ve got you covered with fun last-minute get aways that are just a few hours away. Rescue the holiday weekend with any of these day trips from Chicago. You might even be able to visit two or three!

Bristol Renaissance Faire

Bristol Renaissance Faire

Step back in time to the 16th century at this seasonal fair located just over the Wisconsin border. As you enter the gates you’re transported to 1574 as the town of Bristol celebrates a visit from Queen Elizabeth herself. With twenty stages, nine pubs, jousts, jesters, knights, and faeries, there is something to be seen at every step of this thirty acre park.

Food is reasonably priced, and all entertainment is included. For a more “adult” experience check out one of the pub crawls, filled with bawdy jokes to accompany the beer and mead. The Bristol Renaissance Faire closes on Labor Day for the season, so this is your last chance until next year.

TLTip: See as many stage shows as you can, including MooNie the Magnif’Cent and Adam Crack: Fire Whip. You might also want to get into the spirit by wearing a period costume. Don’t have a suit of armor lying around? You can rent costumes on-site.

  • Hours: Saturday, Sunday, and Monday 10am to 7pm
  • Where: Bristol Renaissance Faire, 12550 120th Ave., Kenosha, WI
  • Admission: $24.50 for adults; $10 children ages 5 to 12

Need a place to stay near Bristol Renaissance Faire: check rates at hotels in Kenosha

Before you go, check more fun things to do in Kenosha

Round Barn Winery “Fruits of Labor” Party

Round Barn Winery

Round the tip of Lake Michigan and head to Baroda, Michigan, this weekend for a “Fruits of Labor” party. Round Barn Winery, Brewery, and Distillery is closing out the summer months with drink specials and food from their grill. While you’re sipping the kids can be jumping in the bounce house or playing yard games.

TLTip: Bring a lounge chair so you can relax and listen to the live music. Rebecca Anne Band and Pop Cult perform on Saturday and Slim Gypsy Baggage and Top Secret Band entertain on Sunday.

  • Hours: Saturday & Sunday 10am to 7pm
  • Where: Round Barn Winery, 10983 Hills Rd, Baroda, MI
  • Admission: $5 entry

Check rates and availability at hotels near Round Barn Winery

Find even more fun in Southwest Michigan

Arthur Amish Country Cheese Festival

Arthur Amish Country Cheese Festival

If you love cheese, glorious cheese, then head south to Arthur, Illinois for the Annual Amish Country Cheese Festival. Located about three hours south of Chicago in the heart of Amish Country, this fest features cheese samples, a tractor pull, a parade, and the International Cheese Curling Championships. That’s right – the sport of curling, with cheese. There’s also a National Cheese Eating Championship. The first to eat a one pound block of Colby wins the prize (which we’re guessing is more cheese). You can also shop Amish vendors and listen to live bluegrass, country, gospel, and music from the 50s and 60s.

TLTip: Explore the town with a walking or audio tour of Arthur. You can pick them up at Wood Loft, which is located on the corner of Illinois and Vine Streets in downtown Arthur.

  • When: Saturday, Sunday, and Monday
  • Where: Arthur, Illinois, off of Route 57 at exit 203
  • Admission: Free

Find a place to stay near Arthur Amish Country Cheese Festival

Milwaukee Rally

You don’t have to own a Harley to have fun at this five day festival. The Milwaukee Rally kicks off Wednesday night and runs all weekend long, through Sunday evening. The rally takes place at dealerships around Milwaukee, including the Harley-Davidson Museum.

There are 88 events at 27 different venues, making this one action-packed, fun-filled experience. Live music includes performances from The Georgia Satellites, Bobby Friss, and The Reverand Horton Heat, as well as appearances by Division BMX High Flying Stunt Team and live tattoo artists.

  • Hours: Through Sunday
  • Where: Multiple locations
  • Admission: Free

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